Amino Acids

, Volume 25, Issue 3–4, pp 295–311 | Cite as

Peroxynitrite reactivity with amino acids and proteins

  • B. Alvarez
  • R. Radi
Review Article


Peroxynitrite, the product of the fast reaction between nitric oxide (NO) and superoxide O2 •− radicals, is an oxidizing and nitrating agent which is able to traverse biological membranes. The reaction of peroxynitrite with proteins occurs through three possible pathways. First, peroxynitrite reacts directly with cysteine, methionine and tryptophan residues. Second, peroxynitrite reacts fast with transition metal centers and selenium-containing amino acids. Third, secondary free radicals arising from peroxynitrite homolysis such as hydroxyl and nitrogen dioxide, and the carbonate radical formed in the presence of carbon dioxide, react with protein moieties too. Nitration of tyrosine residues is being recognized as a marker of the contribution of nitric oxide to oxidative damage. Peroxynitrite-dependent tyrosine nitration is likely to occur through the initial reaction of peroxynitrite with carbon dioxide or metal centers leading to secondary nitrating species. The preferential protein targets of peroxynitrite and the role of proteins in peroxynitrite detoxifying pathways are discussed.

Keywords: Peroxynitrite – Amino acids – Cysteine – Nitrotyrosine – Nitric oxide – Superoxide 


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Copyright information

© Springer-Verlag/Wien 2003

Authors and Affiliations

  • B. Alvarez
    • 1
  • R. Radi
    • 2
  1. 1.Laboratorio de Enzimología, Facultad de Ciencias, Universidad de la República, Montevideo, UruguayUY
  2. 2.Departamento de Bioquímica, Facultad de Medicina, Universidad de la República, Montevideo, UruguayUY

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